Chaetocin A lysine-specific histone methyltransferase inhibitor

Chaetocin (CAS 28097-03-2)

Chaetocin | CAS 28097-03-2 is rated 5.0 out of 5 by 1.
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Synonym: Methyltransferase inhibitor
Application: A lysine-specific histone methyltransferase inhibitor
CAS Number: 28097-03-2
Purity: ≥98%
Molecular Weight: 696.84
Molecular Formula: C30H28N6O6S4
* Refer to Certificate of Analysis for lot specific data (including water content).
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Chaetocin, a natural product originally produced by Chaetomium species, is shown to have apoptotic effects on some cancer cells. Mechanistic studies show that chaetocin is taken up in the cells by a process that requires intact/unreduced disulfides for uptake. Once inside, this compound imposes oxidative stress and consequent apoptosis induction. Other studies have shown chaetocin to reduce lysine-specific histone methyltransferase effects of SUV39H, which play a key role in maintaining stable gene expression patterns during embryonic development and cellular differentiation. Additionally, this agent is reported to cause profound chromatin reorganization in fibroblast nuclei by inducing chromatin condensation/clustering. Consequentially, chaetocin impairs Trx (thioredoxin) systems, which are essential for deoxynucleotide synthesis and involved in a broad range of cellular functions. Chaetocin is an inhibitor of G9a, SUV39H1 and TrxR1.


References

1. Greiner, Dorothea., et al., 2005. Identification of a specific inhibitor of the histone methyltransferase SU(VAR)3-9. Nature chemical biology. 1(3): 143-5. PMID: 16408017
2. Isham, Crescent R., et al., 2007. Chaetocin: a promising new antimyeloma agent with in vitro and in vivo activity mediated via imposition of oxidative stress. Blood. 109(6): 2579-88. PMID: 17090648
3. Illner, Doris., et al., 2010. Remodeling of nuclear architecture by the thiodioxoxpiperazine metabolite chaetocin. Experimental cell research. 316(10): 1662-80. PMID: 20302859

Physical State :
Solid
Derived From :
Chaetomium
Solubility :
Soluble in DMSO (~25 mg/ml), and ethanol (25 mg/ml).
Storage :
Store at -20° C
Density :
~1.9 g/cm3 (Predicted)
Refractive Index :
n20D 1.93
IC50 :
HeLa cells: IC50 = 0.05 µg/ml; HMT SU(VAR)3-9: IC50 = 0.6 µm (Drosophila melanogaster); ortholog: IC50 = 0.8 µm (human); HMT SU(VAR)3-9 : IC50 = 0.8 µm; G9a: IC50 = 2.5 µm; DIM5: IC50 = 3 µm; Lys9-HMTs: IC50 = >90 µm
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
FM3032000
PubChem CID :
11657687
MDL Number :
MFCD00133163
SMILES :
CN1C(=O)[C@@]23C[C@]4([C@@H](N2C(=O)[C@@]1(SS3)CO)NC5=CC=CC=C54)[C@]67C[C@]89C(=O)N([C@](C(=O)N8[C@H]6NC1=CC=CC=C71)(SS9)CO)C

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Certificate of Analysis

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Chaetocin  Product Citations

See how others have used Chaetocin. Click on the entry to view the PubMed entry .

Citations 1 to 3 of 3 total

PMID: # 27924221  Liu, L. et al. 2016. Cell Discov. 2: 16036.

PMID: # 27467759  Das, S. et al. 2016. PLoS ONE. 11: e0160022.

PMID: # 27141211  Rombo, R. et al. 2016. German medical science : GMS e-journal. 14: Doc04.

Citations 1 to 3 of 3 total
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Rated 5 out of 5 by from Lai Lai, YS. et al. (PubMed 25978433) found that Chaetocin, an inhibitor of lysine-specific histone methyltransferase effects, induces differentiation and shows synergistic cytotoxicity with other epigenetic drugs in acute myeloid leukemia cells. -SCBT Publication Review
Date published: 2015-01-13
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